1,2-Diaminocyclohexane, cis- → HCID 90355899, compound

HRID 1470330Notes

Reaction equation

HRID 1470330 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C@@H:11]1([NH2:18])[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[NH2:17]>>[NH2:1][C:2]1[CH:9]=[C:8]([NH:17][C@@H:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C@@H:11]2[NH2:18])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 3429171,2-Diaminocyclohexane, cis-HCID 99421582-Amino-4-fluorobenzonitrile

Product 1

HCID 90355899HCID 90355899, compound

Conditions

Temperature
120 °C

Procedure

A mixture of 2-amino-4-fluorobenzonitrile (5.0 g, 37 mmol) and cis-cyclohexane-1,2-diamine (12.6 g, 111 mmol) was heated to 120° C. After 48 hours, the reaction mixture was cooled to ambient temperature and purified directly via silica gel chromatography (1-5% methanol/dichloromethane, linear gradient) to afford rel-2-amino-4-{[(1R,2S)-2-aminocyclohexyl]amino}benzonitrile. MS ESI calc'd. for C13H19N4 [M+H]+ 231. Found 231. 1H NMR (400 MHz, CDCl3) δ 7.13 (d, J=8.8 Hz, 1H), 6.01 (d, J=9.6 Hz, 1H), 5.85 (s, 1H), 4.68 (d, J=9.6 Hz, 1H), 4.22 (br s, 2H), 3.39-3.34 (m, 1H), 3.14-3.11 (m, 1H), 1.70-1.35 (m, 10H).

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. custompurified directly via silica gel chromatography (1-5% methanol/dichloromethane, linear gradient)

Sources & evidence

ORD record
ord-b6628f0cece243f6ac14247027011ca6
Source dataset
uspto-grants-2015_04
Patent number
US09006444B2

Reaction notes

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